553668-49-8Relevant articles and documents
Coordination of Cu2+ Ions to C 2 Symmetric pseudopeptides derived from valine
Blasco, Salvador,Burguete, M. Isabel,Clares, M. Paz,Garcia-Espana, Enrique,Escorihuela, Jorge,Luis, Santiago V.
scheme or table, p. 7841 - 7852 (2010/11/16)
The acid-base and coordination properties of a family of pseudopeptidic ligands with C2 symmetry derived from valine (4a-e) have been studied using a variety of techniques as a model for metal coordination in peptides and proteins. The Cu2+ cation has been selected for coordination studies, although, for comparison, some results for Zn2+ are also presented. Good agreement has been obtained between the results obtained by potentiometric titrations, spectroscopic analysis, and mass spectrometry (ESI) studies. These results highlight the potential for the use of ESI MS for characterizing the nature of the complex species formed. Clearly, the Cu 2+ complexes are much more stable than the Zn2+ complexes. While the role of the aliphatic spacer seems to be very minor in the case of the Zn2+ complexes, revealing the ability of this cation to accommodate different coordination environments, this role is critical in the case of Cu2+. Different complexes with 1:1 or 2:2 Cu2+:L stoichiometries can be formed according to the length of the spacer and the basicity of the media. This is fully illustrated by the resolution of the X-ray structures of two different Cu2+ complexes corresponding to the ligands containing a spacer with two methylene groups (ligand 4a, complex 6a [Cu2(H-1L)2](ClO4)2 with a 2:2 stoichiometry) and a propylene spacer (4b, complex 5b [CuH-2L] CH3CH2OH with a 1:1 stoichiometry).
New chiral tetraaza ligands for the efficient enantioselective addition of dialkylzinc to aromatic aldehydes
Burguete, M. Isabel,Escorihuela, Jorge,Luis, Santiago V.,Lledós, Agustí,Ujaque, Gregori
, p. 9717 - 9724 (2008/12/22)
A series of chiral tetraaza ligands were studied for the enantioselective addition of dialkylzinc to aldehydes. These bis(amino amide) ligands show high enantioselectivity in the addition of organozincs to aromatic aldehydes. Different structural elements on the ligands seem to play an important role in determining the observed enantioselectivity. Ligand 4b (N,N′-bis(N-l-valinyl)-1,3-diaminopropane, with an aliphatic spacer with 3C atoms) catalyzed the addition of Et2Zn to benzaldehyde, 1-naphtaldehyde, 4-methoxybenzaldehyde, and 4-chlorobenzaldehyde to give the corresponding alcohol products with excellent conversions and selectivities and with enantioselectivities of 99, 97, 98, and 82%, respectively. DFT calculations provide an understanding of the mechanism of the enantioselection process.
Optically active tropocoronands having amino acid residues in linker chains: Syntheses, metal coordination properties, and their abilities as an asymmetric catalyst
Sato, Ohki,Tanbo, Akira
, p. 357 - 366 (2007/10/03)
Optically active tropocoronands (7) having l-amino acid moieties were synthesized by stepwise and one-pot reactions of tropolone derivatives with amino acid linker chains. The coordination styles of their Ni(II) and Pd(II) complexes and the abilities as an asymmetric catalyst were investigated.